City Cruises Chicago: Premier Lunch or Dinner Cruise

Chicago’s skyline looks best from the water, and this cruise gives you a comfortable seat, a plated meal, and a moving view of the city all at once. I especially like the 360-degree observation decks and the way the route brings Navy Pier, Grant Park, the lakefront museums, and Willis Tower into one outing.

The two strongest points are the attentive table service and the party atmosphere once the DJ gets going. Servers such as Leslie have earned praise for being warm and helpful without hovering. The main catch is that the music can get very loud, and the dress code is much stricter than you might expect for a daytime boat ride.

Key points before you book

• Board at Navy Pier: Check in at the Odyssey ticket booth near the Shakespeare Theatre sign, halfway down the south-side dock.
• Three courses at your own table: Lunch and dinner include a starter, main course, and dessert, with some premium dishes costing extra.
• Best views come from outside: Use the observation decks after eating for skyline photos and views across Lake Michigan.
• This is dinner with entertainment: A live DJ and dance floor make the cruise feel more like a floating celebration than a quiet sightseeing boat.
• Dress rules matter: No jeans, shorts, sandals, flip-flops, sleeveless shirts, T-shirts, gym shoes, or tank tops.
• Allow extra time at Navy Pier: Boarding begins 30 minutes before departure, and finding the correct dock takes longer than simply arriving at the pier.

A skyline dinner that keeps moving

City Cruises Chicago’s Premier Lunch or Dinner Cruise is designed around two pleasures: eating well and watching Chicago slide past your window. The Odyssey leaves from Navy Pier and cruises along the Lake Michigan shoreline for about two to three hours.

This is not a narrated architecture tour in the usual sense. You’ll see a strong lineup of landmarks, but the focus is dining, music, and atmosphere. If you want detailed commentary on Chicago’s buildings, you may prefer a dedicated architecture cruise. If you want a special meal with a broad view of the city, this outing makes more sense.

The setting works especially well for birthdays, anniversaries, date nights, and family celebrations. One party used it for a three-month wedding anniversary and enjoyed the sunset view. Another large group of 24 found the meal and service suitable for a shared celebration.

At $88 per person, the price is not cheap, but it covers the cruise, a three-course plated meal, service fee, coffee, hot tea, iced tea, the DJ, and access to the outdoor decks. Alcoholic drinks, souvenir photos, and premium menu items cost extra. I see the value in it when you want one organized evening that combines dinner, entertainment, and sightseeing. It is less compelling if you mainly want a boat ride or a serious food experience.

Finding The Odyssey at Navy Pier

Your starting point is 600 East Grand Avenue, at Navy Pier. Enter through the main entrance, then walk toward the south-side dock. The Odyssey is located about halfway down the dock, near the Shakespeare Theatre sign.

Check in at the Odyssey Lake Michigan ticket booth and collect your boarding passes. The yacht’s name is displayed on the front of the boat and above the booth, but Navy Pier is large enough that you should not leave this until the last minute.

Boarding starts 30 minutes before departure. I would arrive early, especially on a busy weekend or if you need time to park, find the dock, and get through the pier without rushing. One particularly important practical point: check your latest departure information carefully. A past sailing involved confusing messages about the departure location, and the mix-up nearly caused a passenger to miss the cruise.

A ship photographer may offer a photo before you board. You can buy the souvenir later, but there is no obligation to do so.

What lunch and dinner are like on board

Once seated, you’ll have a private table and tableside service. The meal is served in courses rather than as a buffet, which gives the outing a more formal feel and keeps the dining room orderly while the boat is under way.

The menu can change, but the listed lunch and dinner choices include:

• Caesar salad
• Lobster bisque at dinner
• Jumbo shrimp cocktail at dinner for an additional charge
• Mushroom ravioli
• Oven-baked Atlantic salmon
• Roasted chicken breast with rosemary and thyme
• Braised beef short rib
• Pacific cod at dinner
• Filet mignon, striploin, and lobster tails for an additional charge
• Cheesecake, sorbet, fresh fruit, and strawberries
• Chocolate desserts and warm butter cake at dinner

The standard meal gives you a reasonable range of choices, including meat, seafood, and a vegetarian pasta dish. Premium seafood and steak selections can push up the final bill, so check the price before ordering if you are trying to keep the outing near the advertised fare.

The food has generally been a strong part of the experience. Several diners particularly enjoyed the main course and dessert, while one lunch party found the food tasty but not as warm as expected. Another diner liked the salad and dessert more than the chicken. That tells you what to expect: a pleasant event meal, not a destination restaurant.

Service is often the difference between an ordinary meal and a memorable one. Leslie was praised for being attentive, patient, and helpful with suggestions. Other diners also singled out the staff for friendly service. Still, meal timing can slip. One lunch table received its main course after nearby tables had already reached dessert, though the server corrected the problem quickly.

If you have a food allergy, tell your server before ordering. The menu is subject to change, so do not plan your entire booking around one specific dish.

The route from Navy Pier to Willis Tower

The exact view depends on the cruise timing and conditions, but the route is built around Chicago’s major lakefront and downtown landmarks. You should think of the listed stops as sightseeing viewpoints from the boat, not shore visits.

John Hancock Center and Water Tower Place

Early in the route, you’ll see the John Hancock Center and Water Tower Place. The John Hancock Center is one of the most recognizable vertical markers on Chicago’s North Michigan Avenue skyline.

Water Tower Place gives you a sense of how quickly the city shifts from lakefront recreation to dense shopping and high-rise development. From the boat, these buildings help you read the shoreline as a whole rather than seeing them as isolated attractions.

Lake Point Tower and Navy Pier

Lake Point Tower is especially easy to appreciate from the water because its position near the shoreline gives you a clear look at its unusual shape and setting. It is a useful reminder that Chicago’s architecture is not limited to the downtown office towers.

Navy Pier appears as both your departure point and one of the route’s visual anchors. From Lake Michigan, the pier’s length and position make more sense than they do from the land. It also gives you a good perspective on how much activity is concentrated along the lakefront.

Aon Center, 311 South Wacker, and Crain Communications Building

The Aon Center is one of the clean, tall forms in the central skyline. The view from the lake gives you distance, which helps you take in the full height of the building instead of looking up from a downtown sidewalk.

You may also spot 311 South Wacker and the Crain Communications Building. These buildings help fill out the city’s architectural profile, but the cruise does not promise a detailed explanation of each one. If you want to know who designed them or how they fit into Chicago’s architectural story, bring your own guidebook or choose a dedicated architecture tour.

Shedd Aquarium and Adler Planetarium

The cruise’s view of Shedd Aquarium and Adler Planetarium is one of its best stretches for understanding Chicago’s Museum Campus. Both buildings sit by the water, with the skyline rising behind them.

From the lake, you get the reverse of the usual city view. Instead of standing near the museums and looking toward downtown, you look back at the museums with the towers beyond them. That angle is especially useful for photographs, since it combines low, historic-looking waterfront buildings with the tall central skyline.

CNA Center and Willis Tower

The CNA Center and Willis Tower round out the downtown view. Willis Tower is the most obvious landmark in this part of the route, but distance changes its character. From the boat, you see it as part of a dense group of towers rather than as a single attraction.

The cruise does not stop at these buildings. The value is the changing angle as the boat moves, plus the chance to photograph several well-known Chicago landmarks in one continuous outing.

The outdoor decks are the real sightseeing seat

The dining room is convenient for the meal, but I would not stay indoors for the whole cruise. After your courses arrive, head to the outdoor observation deck for the broadest views.

The deck offers a full sweep across the skyline and Lake Michigan. You can take photos without a window reflection, watch the shoreline recede, and see how the city’s towers group together from the water. On a clear evening, this is the part that makes the outing feel distinctive rather than simply being dinner in an unusual venue.

Weather matters. A cold-weather sailing can make the upper deck uncomfortable, even if the interior remains pleasant. In November, one diner found the top deck too chilly for extended sightseeing. Bring an extra layer when the forecast is cool, and do not assume that a dinner cruise guarantees warm outdoor conditions.

The interior deck is available if the wind or temperature turns unpleasant. You can move between indoor and outdoor spaces, but the best photos usually require a short stay outside.

The DJ changes the tone after dinner

The live DJ and dance floor make this a social evening rather than a quiet restaurant with windows. Music plays during the cruise, and you can dance after your meal or simply sit back with a drink.

This works well for birthdays and group celebrations. A DJ helped create a party feel during one birthday outing, and another celebration used the music as a reason to return. If you like a lively setting, this is a major benefit.

The tradeoff is volume. Music has been too loud for some diners, making conversation difficult. Children may also use the dance floor, which can change the mood from polished dinner to family party. For a quiet anniversary meal, request or choose a seating area away from the main dance action if that option is available, though the information provided does not guarantee specific seating locations.

Alcoholic drinks are available for purchase. Coffee, hot tea, and iced tea are included, which is useful if you want to keep extra spending under control.

Dress for the dining room, not the beach

The dress code is smart-casual, with jackets and cocktail attire strongly suggested for dinner. The rules are more specific than the usual smart-casual language: jeans, shorts, sandals, flip-flops, sleeveless shirts, tank tops, halter tops, T-shirts, gym shoes, and sports shoes are not allowed.

Take this seriously. You are boarding a dining boat, not a casual sightseeing ferry. A neat outfit will also fit the setting better, particularly for an evening sailing, anniversary, birthday, or special dinner.

Smoking is not permitted indoors. Smoking is allowed on the outdoor observation decks.

The cruise is wheelchair accessible. Infants are free, but you need to select the free infant ticket when booking. If you are booking for a group, make one reservation for everyone. Separate reservations may not be seated together.

What the $88 price really buys you

The fare makes the most sense when you place a value on convenience. For $88, you receive a cruise of roughly two to three hours, a three-course meal, table service, onboard entertainment, and access to skyline views that would otherwise require separate planning.

You are also paying for the occasion. The boat provides a ready-made setting for a birthday or date night, so you do not need to arrange dinner, a skyline viewpoint, and evening entertainment separately.

Still, several costs can appear on top of the base fare. Drinks are extra, premium menu items cost more, and souvenir photos are for sale. If you add cocktails, steak, lobster, or multiple photos, the final amount can climb quickly.

I would book this for a special occasion or for a first visit when you want a broad introduction to Chicago from the lake. I would skip it if your priority is low-cost sightseeing, architectural commentary, or a chef-focused meal.

Who will enjoy this cruise most?

You are a good match if you want:

• A special meal with a city view
• A celebration with music and dancing
• A comfortable way to see several landmarks from the lake
• A plated meal instead of casual counter service
• Outdoor photo opportunities from a moving boat
• A two to three-hour activity with a clear start and finish

You may want another option if you need a quiet dinner, dislike formal dress rules, or want detailed architectural narration. The cruise includes an English-speaking guide, but the main focus is the meal and onboard atmosphere, not a running lecture about every building.

The experience also depends on timing. A sunset sailing can add romance and softer light, while a daytime lunch gives you clearer views for spotting buildings. The supplied information does not guarantee a particular sunset time, so check the departure schedule before booking.

Should you book City Cruises Chicago?

I would book this cruise if you want Chicago sightseeing wrapped inside a celebration. The combination of plated dining, friendly service, skyline views, and a DJ gives you more than a standard boat ride, though it also makes the experience less quiet and less focused on architecture.

Choose dinner for a dressier, more romantic evening, especially if you want the music and dance floor. Choose lunch if you prefer daylight views and a more relaxed pace. Arrive at least 30 minutes early, dress properly, check the departure details, and save time after the meal for the outdoor deck.

At $88, it is fair value for a special outing, not a bargain attraction. The food and service are generally well received, but delays, temperature issues, loud music, and occasional onboard problems can happen. If those limits fit your expectations, this is a polished way to see Chicago from the water without planning every detail yourself.

FAQ

Where does the City Cruises Chicago Premier Cruise depart?

The Odyssey departs from Navy Pier. Enter through the main entrance, walk along the south-side dock, and find the Odyssey Lake Michigan ticket booth near the Shakespeare Theatre sign.

How long does the cruise last?

The cruise lasts about two to three hours. Check the available departure times when booking.

What is included in the ticket price?

The ticket includes the lunch or dinner cruise aboard The Odyssey, a three-course plated meal, onboard DJ and dance floor, unlimited coffee, hot tea and iced tea, and the service fee.

Are alcoholic drinks included?

No. Alcoholic drinks are available for purchase onboard.

What food choices are available?

The menu includes starters such as Caesar salad, with lobster bisque and other premium seafood choices available at dinner. Main courses can include mushroom ravioli, salmon, chicken, short rib, and other dinner selections. Dessert choices include cheesecake, sorbet, fruit, and additional dinner desserts. The menu may change.

What should I wear?

Wear smart-casual clothing. Jackets and cocktail attire are strongly suggested for dinner. Jeans, shorts, sandals, flip-flops, sleeveless shirts, tank tops, halter tops, T-shirts, gym shoes, and sports shoes are not allowed.

Is the cruise wheelchair accessible?

Yes, the activity is wheelchair accessible.

Can infants join the cruise?

Yes. Infants are free, but you must select the free infant ticket option when booking.

Can separate bookings be seated together?

The provider cannot guarantee that separate reservations will be seated together. Make one reservation for your full party if you want to sit together.